If you know the mass of the hole, yes, you can predict how much time will elapse on your clock between now and when you hit the singularity.
> Does the person falling (for the sake of this example let's assume they maintain consciousness) experience the passing of time as they fall further "into" the black hole?
Yes.
> If so, how long would one experiencing the falling until they reach the singularity?
A reasonable estimate for free-falling into a black hole is that the time to reach the singularity is the 3/2 power of the radial coordinate you are falling from, in units of the hole's Schwarzschild radius. If you are just crossing the hole's horizon, you are at the hole's Schwarzschild radius, so your time to reach the singularity from there would be that radius divided by the speed of light (to convert to time units instead of distance units). For a hole of 10 solar masses, for example, this time is about 100 microseconds (Schwarzschild radius of about 30 kilometers divided by the speed of light).
There is no such thing. Speed is not absolute in relativity. You can only meaningfully talk about your speed relative to some particular object or observer, and then, strictly speaking, only when you and that object or observer meet (i.e., your worldlines cross).
Similar remarks apply to all of your questions; they simply aren't meaningful.
My instinct is that the observer would subjectively experience it to take exactly the time predicted by classical mechanics to “hit” the singularity — basically that all the considerations above would cancel out in the local reference frame — but that to an outside observer it would take an infinite amount of time.
None of these things are useful in the case under discussion. 1) is invalid--the singularity is a moment of time, not a place in space, and you aren't "accelerating towards" it. 2) is not well-defined inside the horizon (spacetime curvature is, and does increase without bound as you approach the singularity, but that's not quite the same as "gravity"). 3) is a special relativistic effect on others observing you; you yourself don't experience any "distance compression" regardless of your state of motion.
Also, you can accelerate towards the black hole singularity and get there faster.